Methanesulfonyl chloride → 3-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

HRID 1504844ノート

反応式

HRID 1504844 の反応式
[OH:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH:3]([NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])[CH2:4][NH:5][C:6]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:15])(=[O:27])=[O:26]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 755959732-(Boc-amino)-3-(Cbz-amino)-1-propanol

生成物 1

HCID 867317143-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of benzyl tert-butyl (3-hydroxypropane-1,2-diyl)biscarbamate (60.0 g, 185 mmol) in DCM (1000 mL) was added methanesulfonylchloride (23 g, 200 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 12 hours, the reaction mixture was concentrated under reduced pressure and purified directly by chromatography on silica gel to give 3-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate. MS ESI calc'd. for C17H27N2O7S [M+H]+ 403. found 403. 1H NMR (400 MHz, CD3OD) δ 7.34-7.32 (m, 5), 5.17-5.07 (m, 2H), 4.18-4.16 (m, 2H), 4.09-3.91 (m, 1H), 3.29-3.28 (m, 2H), 3.05 (s, 3H), 1.42 (s, 9H).

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified directly by chromatography on silica gel

出典と根拠

ORDレコード
ord-ce87acb0f6984965ac41d9863995ff7e
出典データセット
uspto-grants-2015_12
特許番号
US09216173B2

反応ノート

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